


Because Dresses Work

by DesertHeart



Category: Supernatural
Genre: Cross-Posted on FanFiction.Net, Cross-Posted on Tumblr, M/M, Sex, Weecest, Wincest - Freeform, bad depiction of anal sex, cross dressing, judge free zone lol
Language: English
Status: Completed
Published: 2017-11-28
Updated: 2017-11-28
Packaged: 2019-02-08 04:02:25
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,667
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12856317
Author URL: https://archiveofourown.org/users/DesertHeart/pseuds/DesertHeart
Summary: Written several years ago. Not my best work but it is a work. I thrive on admiration though so feel free to comment or let me know what you think.





	Because Dresses Work

It had been another long night as Dean had driven the two of them to yet another town. The moment Dean had turned 16 dean had been given the keys to the car and Sam and sent away. Even though Sam was quite a bit older now they still weren't allowed on the scene when dad was hunting. And now that they were older they rarely saw him. Used to they would see him when he came to drive them to other areas but now Dean handled all of that. Sam sighed as he sat on the bed in the newest hotel. He had his crappy laptop on his lap as he slowly downloaded his school files. Maybe they would be here long enough for a proper school? And maybe a friend? He shook his head. Wistful thinking. Dean had gone out to get dinner and Sam looks up when he hears the door open.

Dean had managed to find a nearby diner for food. He thought Sam deserved something better than Lucky charms and canned food so Dean took some of the money he got from hustling pool and bought himself a bacon cheese burger with fries, and got Sam a salad and fries, and got the both of them milkshakes. Dean knew Sam wasn't happy about moving to another crappy hotel so hopefully a good meal would cheer him up. "Dinner, Sammy come and get it. I got you a salad. You're such a health freak." Dean joked.

"I'm not a health freak Dean. It keeps your body healthy and in shape and thus you can move faster and have a higher chance of living." Sam argued from his spot as he slowly unfolded from the bed. He was 16 and still in that awkward stage where his body didn't always feel even, like his legs were to long for his body, but he still managed to be more graceful than his brother. He sighs at his old laptop. How was he supposed to pass high school with this? He turns to him, "Don't call me Sammy. Don't you think I'm a bit old for a silly name like that?" He knows it's useless to say this but it is habit by now and they have been bantering over this for a few months now. He walks over to him, "Thank you for getting dinner."

Dean grinned. The reason that Dean called Sam Sammy was because Dean felt like it was sign of closeness. Dean liked getting Sam flustered about it. "You're welcome Samantha. Tomorrow we'll go down to the school and get you registered and everything ok? I know much how you love school."

Sam stopped and scowled at him from his place, "You know that's not my name. Or my sex. Why do you insist on saying those things?" He grabs the salad and returns to the laptop. "We can't register me if this damn laptop won't download my information. It has way too many viruses and junk clogging it up."

"Aww Sam come on. I'm just teasing." Dean new that Sam's laptop had been giving him a lot of trouble. Dean had been saving his money to get Sam a new laptop for Sam. He almost had enough saved up. Dean figured he could give Sam the laptop for Christmas but that was a month away. If Dean got the money maybe Sam would get his Christmas present early. "It'll be ok Sam." Dean ruffled Sam's hair playfully. "You should take your nose out of a book everyone in a while. Now that you've grown like a weed. I be the girls will be all over you." Dean teased.

Sam rolled his eyes at him. "I don't have time to mess around with girls. I am still in school and it's very important I get a high GPA despite all this moving around." he says scowling at the laptop as he tried get it to work. He was watching it when it randomly shuts down, "Really? Are you kidding me?" He says picking it up and trying to turn it back on then sighing and just abandoning it on the table with a huff. "I'm going to have to find a library to download and print them." He doesn't even respond to the ruffling that was how frustrated he was with the laptop. He turns to the other, "What are you supposed to be doing here while I am at school?" he asks. Even though he was 16 now he hadn't really been trained in the weaponry that his brother had been. Theory chants and books? Finished. But they didn't seem to want him to physically fight.

"Just the usual things. You know take care of you." Dean grabbed the keys off the counter "I think the library is still open. I'll drive you alright?" Dean knew that Sam wondered why he hadn't really learned the physical side of hunting. Dean admitted he was nervous about it. Once Sam learned the physical side he would be out hunting. Dean didn't know what he would do if anything happened to Sam. Dean knew he would have to start teaching Sam things. Hopefully, Dean could give Sam more time to be a kid.

Sam never told Dean but he hadn't felt like a kid for a long time. He knew his life was a lot different than most peoples and he had never even tried to be a normal child. He would have to carve out normalcy for himself later on. But he wasn't sure he wanted normalcy. Granted a good portion of things he wanted weren't exactly correct. "Alright, thank you Dean." He says pushing aside his half eaten salad. He ate less when he was frustrated. He glared at the laptop once more before turning to follow Dean. He frowned, Dean was being really sweet tonight. He must be planning to hang out at the bar tonight.

Dean had planned on going out tonight but, wasn't so sure about leaving Sam all by himself. Dean frowned noting that Sam barely ate. "You should eat more when we get back alright Sam?"

Sam nods, "Alright, I will once I have the things I need." He says to the other not really paying attention to what he was saying and heads out to the car.

Dean sighs and follows Sam. The kid had been really mood lately. Dean wondered if there was something else on his little brother's mind besides school and his laptop. Dean started up the impala and began to sing-off key to one of his favorite songs. Finally when they pulled up the library Dean asked "Is there anything else wrong Sam? You can talk to me you know that."

Sam had been silent as he had sung horribly. His brother couldn't carry a tune if it killed him. He looked up when he speaks to him. "Um, no I think I am fine." he says softly to the other. He couldn't tell him the thoughts running through his mind. It would hurt the other, and one would horrify him he is sure.

Dean prided himself on knowing his baby brother better than anybody. Dean saw Sam sad expression and became concerned. Sam was hardly ever like this. "Think your fine Sammy? It's alright whatever it is. I'll never hate you Sammy not matter what you say to me."

Sam smiles at him, "I know Dean. How could you? You are practically my parent, or maybe that is why you should hate me?" he muses to himself before shaking his head and getting out of the car.

Dean placed a hand softly on Sam's shoulder. "Why should I hate you? You're really scaring me Sammy." Dean wonder why Sam thought Dean would hate him. If anything it should be the other way around.

Sam glanced back at him and smiles, "Don't worry about it Dean. I am just worried about school. Come on let's go and take care of this ok?" He says softly as he heads up to the library.

Dean decides to let it go for now. Dean follows Sam into the library and waits for Sam to finish what he needed to do.

Sam signs in with the fake names he has to use and he sighs as he heads over to the computers and waits for the super slow things to load up what he wants. He thinks about the fact that Dean had called him Samantha earlier, did he wish he was a girl? He shook his head that was foolish. He starts to tap his fingers as he waits.

Dean glanced over at Sam and bit his lip. He felt bad about his un-brotherly feelings for Sam. Maybe it was because of how they were raised or something. Maybe it was genetics who knows. Dean had tried to get rid of his feeling. He found himself picking girls or guys that looked like his brother. Dean shifted slightly. Dean had wanted to stay with Sam but, he couldn't. Dean hopped he could find someone to take his frustrations out on at the bar.

The file eventually loads and Sam smiles a little as he hits print. "Do you have a few dollars? It costs to print here." He says. He was never allowed to carry the money. He guess Dean thinks he would take off if he did. But Sam would never leave. He loves his brother too much. He would be a girl if he wanted him to be. He would do anything.

"Yeah Sammy." Dean stood up and reached for his wallet trying to hide his straining erection. Dean reaches into the wallet and hands Sam the money.

Sam smiles up at him, "Thank you Dean." He says sweetly before turning to go and purchase the papers from the librarian. When he gets the papers he returns and gives him the change with a smile.

God that smile! Dean mentally groaned thinking about Sam smiling up at him for a different reason. Dean struggled to push those thoughts away. Dean smiled back at Sam. "Let's get back. I want you to finish that salad and that rest of the food ok?"

Sam rolled his eyes at him turning and heading back to the car. "And if I am not that hungry?" He asks he wished he wouldn't always seem so worried about him because it made him want Dean to worry about him with something different.

"You're always hungry Sammy. You hardly ate today." Dean knew he worried about Sam. It was only about love. "I'm going out for a little bit when get back. Alright Sam." Dean waited for his brother's reaction. Hoping he could figure out what was wrong.

Sam looked down as he got into the car. "Alright. Will you be staying with someone else tonight? If so I will lock up fully when you leave." He answers ignoring the way his heart clenched angrily in pain and jealously. How did he make Dean want him? But he was a good liar so he wouldn't know.

Dean heard the pain in his little brother's voice when he asked that. Maybe, Sammy wanted him the same way Dean wanted him. Dean shock his head he couldn't think that way. "I don't think so Sammy. I won't be gone that long. Promise."

"Alright I can handle that." Sam says as he watches the scenery. It was already getting dark. So Dean was planning on a quickie with some whore. He could handle that. It wasn't a long time girl. Not this time.

Dean made sure that Sam was nice and settled before heading out to the bar. Dean decided he would pick up some cash at the bar for Sammy's new laptop and see if there was any action. If not Dean could always go home and jack off in the shower.

Sam on the other hand calculated how long he had till the other get back and pocketed his knife and the money he went out and 'earned in various places with various ways and headed out. If Dean wanted a girl so bad he would see what he could give to him.

Sam just follows the scantily dressed people of the town till he hits the red-light district and starts searching for a proper shop to get what he believes he needs. He picks out a dress that is black and in the style he thinks Dean likes with matching shoes and stockings and one of the others suggests he gets hair piece. He flushes and lets the other help him. They help him pick everything out to make him the most beautiful he can be and help with make up as well. When finished he heads to the only bar in the small town.

Dean smiled the people at this bar were really easy to rip-off. Dean found nobody he was really interested in and decided to step outside of the bar. Outside the bar a woman with chin length brown hair and the same color eyes as Sam is leaning against a wall smoking a cigarette and wearing slutty clothing, she shoots a smile at dean, "Hello sweetheart."

Dean swallowed nervously at the "women" leaning against the wall. Dean would know those eyes and his little brother's voice anywhere. "Sammy?" Dean asked. Dean noticed a few people staring at Sam. Dean wanted to get him out of here fast and back to the hotel. Dean knew it was wrong, if Sam wanted it too then it was fine. Dean was probably going to hell anyway. Dean vowed that he wouldn't force Sammy into doing anything he didn't want to.

Sam flushed a little, but the people had helped him do this. Told him how to walk and talk and make sure he was desirable to the other. He pushed off of the wall. There was no turning back now. He had to do this now. He walked towards the other and wraps his arms around his neck and dropping the cigarette to the ground, it had been disgusting but it was supposed to add to sexuality or something. The dress swooshes around his legs, "Yes?" He purrs at the other. He had noticed the other people watching him and was a little nervous. Ok, this whole situation was making him nervous. But he couldn't back out now. He just hoped that he had been right and this was what he wanted.

"Always knew you'd be a pretty girl Sammy. Didn't have to dress up for me though I would have liked you either way. Can't wait to get you back to the hotel." Dean pretty much drags Sammy to the impala.

Sam smiles up at the other thrilled. "Really?" he says hope surging threw his body. He was right. He had done it right. Dean wanted him! He gets in and slides his hand on Dean's leg.

Dean felt his heart swell when Sam's face lit up. "Yeah, Sammy I love you." Dean speeds back to the motel. Thinking about all the things he wanted to do Sammy.

"Dean, I love you to." He says softly to the other. He wanted Dean to do things to him. He rubs a little at the lipstick on his lips. Maybe he should put on more? He wasn't sure.

Dean could tell that Sam was nervous. "It's O.K. Sammy you look great. I know you're nervous just let me help ya. If you feel uneasy make sure you tell me that you want me to stop." Dean says as he parks the impala and carries Sam inside the motel and sets him down on the bed kissing him softly.

Sam nods and holds onto the other tightly his stomach flipping when the other kisses him. His eyes flutter shut and he kisses back. It was his first kiss and it was amazing.

Dean pulls Sam on top of him kissing in some more before breaking away. With one hand up the younger's shirt Dean asks "Well how was it?"

Sam flushes looking down at him, "Amazing. Did you lock the door?" he asks body sweating and he is hard. He wants the other to do more. But he isn't sure how to make the next move.

"Yeah it's locked don't worry doubt anybody's coming in anyway." Dean slowly slips Sam's shirt off. Dean knew Sam didn't really know what do. "Alright Sammy what do you want to do next? You can touch me if you want."

Sam flushed and reached a hand out to slip up his shirt. The skirt was riding up and it made him a little nervous because it doesn't cover anything anymore. He pushes the shirt up looking at his brother. He has seen him naked plenty of times but it was different now.

Dean lets out a smirk and guides Sam's hands and his chest. Dean takes one hand and gives Sam's butt a playful smack and squeeze before grabbing the skirt and pulling it down tossing it on the floor.

Sam shivers and touches him face now redder than ever. He feels exposed so tries to pull off the others search to make it easy. The boots he was wearing were healed and laced up. He starts to push them off and he reaches a hand down to pull the laces off.

Dean watches Sam remove his boots and smiles. Once Sam gets the boots off Dean pushes Sam down on the bed and climbs on top of him kissing every part of Sam, Sam's lips, neck everywhere. Dean licked on of Sam's nipples while his hands roamed everywhere.

Sam was shocked and cried out in surprise when he did this but then moans as his body reacts to the others touches and his erection strains against the stockings and lacy panties. Dean's hands touch the leather pouch on his thigh where he hid his knife.

Dean takes out his knife and uses one hand to grip the side of Sam's panties and slices them off with the knife. Dean toss them and uses one hand to jerk Sam slowly.

Sam starts to moan loudly and his hands are shaky as they reach to attempt to pull down dean's zipper to return the favor. Why hadn't he done this sooner? He could have saved himself a lot of pain.

Dean helps Sam pulled down the zipper and guides Sam's hand to his cock. Dean reaches back in his pocket to pull out some lube. Dean coats the lube on his finger and softly pushes one in Sam's whole while his other Dean is jerking Sam off.

Sam lifts his legs for easier access as his body adjusts to the strange sensation and he jerks off his brother. He hums a little in between the moans. He wonders what else would happen. He had researched quite a bit and new what would happen but he had no experience with it so it was all new and fascinating.

"God, Sammy you so hot. All pretty and flushed." Dean adds another finger moving around to find Sam's prostate. "Gonna have to work you open good. Hmmm so tight Sammy." Dean says huskily.

Sam moaned louder at the others sexual words. He enjoyed the others words and he wanted more and when he touched his prostate his eyes shoot open and he moans loudly unable to articulate how amazing he feels.

Dean "Feels good huh Sammy." Dean adds another finger and begins to pump a little faster. "Gotta relax for me alright Sammy? So tense."

Sam nods his head and forces his body to relax even though his body was trying to tense against the others intrusion.

"Good job Sammy." Once Dean Feels that Sam is lose enough Dean withdraws his fingers and places his hands on Sam's hips. Dean leans down and kisses Sam. "It's going to feel a little weird and it's going to hurt, but it'll feel good alright?"

Sam shudders and closes his eyes forcing his body to relax even more. "Alright. I can do it." He breathes out ready to take all Dean can give.

Dean slowly slides himself into his little brother. Dean feels his brother tense up. "Shh I know Sammy." Dean lets his brother adjust to his long thick length. Dean kisses his brother's cheeks and whispers words of encouragement. Dean slowly begins to pump in and out of his brother. "Prefect. Wanted you for months Sammy." Dean moans.

Sam shudders body in pain as he tries to force himself to adjust he is glad the other waits for him to adjust because it felt like he was on fire. But the pumping helps and soon it feels good and he is able to push back a little letting him know he can move.

"That's it move with me Sammy." Dean moves until he finds his brother's prostate. Dean moves loudly feeling his climax beginning to build.

Sam moves with him not even minding the silly nickname that he was using. It was almost endearing here. When he hits the prostate he moans loudly body shuddering as he gets near his climax.

Dean moves his hand to Sam's cock and pumps it while he moves. Dean and his brother reach their climaxes at the same time. Dean collapses on to his little brother. Dean slowly pulls out of his brother and then pulls in his little brother on top of him and wraps his arms around him. "I love you Sammy."

: Sam snuggles into his chest and nuzzles him. "I love you too, Dean." He says softly to him. "I have for a long long time." He says again.

Dean kisses Sam again. "Let's get some sleep Sammy." Dean wraps the blanket around the both of them.

Sam cuddles and smiles "Yeah, let's sleep. I have a lot of work at the school tomorrow."

Dean closes his eyes and smiles.


End file.
